Chemistry:5α-Hydroxylaxogenin

5α-Hydroxylaxogenin
Identifiers
	IUPAC name (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18R)-16,18-dihydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-19-one;
CAS Number	56786-63-1;
PubChem CID	69906537;
ChemSpider	35228242;
UNII	844KE20WT5;
Chemical and physical data
Formula	C27H42O5
Molar mass	446.628 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC(=O)[C@@]6([C@@]5(CC[C@@H](C6)O)C)O)C)C)OC1;
	InChI InChI=1S/C27H42O5/c1-15-5-10-27(31-14-15)16(2)23-21(32-27)12-20-18-11-22(29)26(30)13-17(28)6-9-25(26,4)19(18)7-8-24(20,23)3/h15-21,23,28,30H,5-14H2,1-4H3/t15-,16+,17+,18-,19+,20+,21+,23+,24+,25-,26+,27-/m1/s1; Key:HCRGPOQBVFMZFY-PPCFKNSFSA-N;

Short description: Chemical compound

5α-Hydroxylaxogenin is a chemical compound which is a semi-synthetic derivative of laxogenin, found in the Chinese medicinal plant Smilax sieboldii.^[1] It acts as a partial agonist at androgen receptors and has been sold as a bodybuilding supplement and pre-workout product.^[2]^[3]

References

↑ "Steroidal Saponins from the Genus Smilax and Their Biological Activities". Natural Products and Bioprospecting 7 (4): 283–298. August 2017. doi:10.1007/s13659-017-0139-5. PMID 28646341.
↑ "The power of hyphenated chromatography-Time of flight mass spectrometry for unequivocal identification of spirostanes in bodybuilding dietary supplements". Journal of Pharmaceutical and Biomedical Analysis 167: 74–82. April 2019. doi:10.1016/j.jpba.2018.12.045. PMID 30753977.
↑ "Androgenic properties of the dietary supplement 5α-hydroxy-laxogenin". Archives of Toxicology 96 (7): 2139–2142. July 2022. doi:10.1007/s00204-022-03283-5. PMID 35344071.

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[pmid28646341-1] "Steroidal Saponins from the Genus Smilax and Their Biological Activities". Natural Products and Bioprospecting 7 (4): 283–298. August 2017. doi:10.1007/s13659-017-0139-5. PMID 28646341.

[pmid30753977-2] "The power of hyphenated chromatography-Time of flight mass spectrometry for unequivocal identification of spirostanes in bodybuilding dietary supplements". Journal of Pharmaceutical and Biomedical Analysis 167: 74–82. April 2019. doi:10.1016/j.jpba.2018.12.045. PMID 30753977.

[pmid35344071-3] "Androgenic properties of the dietary supplement 5α-hydroxy-laxogenin". Archives of Toxicology 96 (7): 2139–2142. July 2022. doi:10.1007/s00204-022-03283-5. PMID 35344071.

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Identifiers

IUPAC name (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18R)-16,18-dihydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.0^2,9.0^4,8.0^13,18]icosane-6,2'-oxane]-19-one
CAS Number	56786-63-1
PubChem CID	69906537
ChemSpider	35228242
UNII	844KE20WT5
Chemical and physical data
Formula	C₂₇H₄₂O₅
Molar mass	446.628 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC(=O)[C@@]6([C@@]5(CC[C@@H](C6)O)C)O)C)C)OC1
InChI InChI=1S/C27H42O5/c1-15-5-10-27(31-14-15)16(2)23-21(32-27)12-20-18-11-22(29)26(30)13-17(28)6-9-25(26,4)19(18)7-8-24(20,23)3/h15-21,23,28,30H,5-14H2,1-4H3/t15-,16+,17+,18-,19+,20+,21+,23+,24+,25-,26+,27-/m1/s1 Key:HCRGPOQBVFMZFY-PPCFKNSFSA-N

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